Matt McLeod | My 2019 Retrospective (And 2020 Action Plan)
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My 2019 Retrospective (And 2020 Action Plan)

Want the audio version? Click here.

A one-hour exercise to help you celebrate your biggest wins, identify your biggest opportunities, and dominate the new year.

In NYC earlier this year as a beautiful sunset hits the Empire State Building.


What’s super cool about the Internet and technology today is the creative ability to document your life. We have podcasts, YouTube, social media, blog posts, and a smart phone with way too many pictures and videos hogging up memory space.

My kids (and your kids) are going to be able to see every major moment of your life, if you choose to capture it.

To me, that’s exciting. There would be nothing cooler than to go back in time and read my mom or dad’s blog about how their year went in 1993 (the year I was born). So, to my future kid reading this, I hope this retrospective exercise is cool to you.

On a more selfish note, I plan on doing these retrospectives each year to serve as one big journal entry (I got the idea from my friend and mentor, Nate Green). I can see what problems I was having, where my headspace was, and fun experiences I had since forgotten about.

Not to mention, I can see if I’m still tolerating my same bullshit year after year.

What’s a retrospective?

A retrospective is when you look back on past events to identify what worked…and what didn’t work. A retrospective helps you celebrate your wins and identify your weaknesses. It helps you learn from the past and correct for the future.

How to do your own personal retrospective

To do a personal retrospective, you simply pick a particular project or time period and ask yourself the following questions:

  • QUESTION 1: What’s working? (“What did I do right? What am I proud of?”)

  • QUESTION 2: What’s not working? (“What could be improved? What are my biggest opportunities for growth?”)

  • QUESTION 3: How can I fix what’s not working for a better result? (“What specific things can I focus on next time?”)

Then you spend 15-30 minutes writing about each.

My 2019 Retrospective

To show you how it’s done⏤and to hopefully encourage you to do the same⏤I’ll share mine with you.

QUESTION 1: What’s working? (“What did I do right? What am I proud of?”)


I started online fitness coaching during my junior year in college, about 4 years ago. After getting my Bachelor’s in Dietetics, I had to earn 1400+ hours of experience through my dietetic internship and then pass my board’s exam to become a Registered Dietitian. I did coaching on the side, but I was never able to put 100% effort into my business.

I passed my RD exam (pic below) in December of 2018, which made 2019 the first year of going all-in. It was time to see if I had the balls to support myself – I’m proud to say I did (so far).


I’ve always prided myself on working hard. It’s a controllable variable and it allows me to get ahead of the more talented people who don’t work as hard. But there comes a point of diminishing returns and there’s no reason to work harder for the sake of working harder.

The question I keep returning to: “What’s it all for? What’s the point of all this stress, anxiety, and overwhelm I’m succumbing myself to?”

I’m not KILLING it by any means, but I’m doing okay. I can pay my rent, my bills, and for a fancy steak dinner here and there. Plus, I’m doing what I love every day. Life is good.

It took me a while to admit this, but I’m okay with not being the best. I don’t need to be a millionaire to be happy or to feel successful as a man. I’m healthy, my family is healthy, I have meaningful relationships, I live comfortably, and I’m doing challenging work I love that helps people like me – I’m enjoying myself.

And I refuse to beat myself up and not fully experience my present moment because I’m not like him, her, or the other guy. I don’t want the pressure that comes with the astronomical expectations of keeping up with the Joneses.

Fuck that. I’m proud of who I am and who I’m working to become. I hope you are too.


  • My podcast has allowed me to have long, un-interrupted, genuine conversations with people I look up to and care about.

  • I was able to work 1:1 with my long-time man crush, Nate Green (again, the inspiration behind this whole post).

  • I traveled to New York City, Philadelphia, Chicago, Myrtle Beach, Nashville, Columbus, and more to hang out with friends and family.

  • I had a weekend retreat at Red River Gorge with some very close friends and complete strangers – we hiked, stayed in a tiny cabin together (8 grown dudes), and spent the majority of our time sitting in lawn chairs, talking in a creek.
  • My girlfriend and I have gone through the struggles of long distance (she’s in NY, I’m in KY), but I genuinely feel we’re the closest we’ve ever been.

  • I was able to buy my parents dinner at a fancy restaurant for the first time ever.

  • I found out my older brother is going to have a baby and I’m gonna become a Funcle (Fun Uncle). 


If there’s only one thing you take from this retrospective, make it this: start and end your day with a laugh.

I’ve realized I’m down for a Silly Goose Time and that’s it, dude.

Some comedians you should check out (I’m just linking their Instagram’s):

Me and Chris D’Elia at his comedy show in Lexington.

QUESTION 2: What’s not working? (“What could be improved? What are my biggest opportunities for growth?”)


Learning from others has been the foundation to how I navigate my life ⏤ family, books, and mentors (including Internet mentors) are my main compass. Without question, they have accelerated my growth by allowing me to filter through 95% of shit that doesn’t matter.

This can be a slippery slope, however, because when I mimic others I lose some originality. I forget to think for myself because I’m blinded by my admiration for a particular role model. I feel like I’m “supposed to” do something because they did it, too.

Basically, I’m trying to be someone I’m not.

I’ve already accepted the fact that I’m not ever gonna be the smartest, the prettiest, the most famous, the wealthiest, the whatever.

But I’m starting to realize there’s one (albeit cheesy) thing I can do that no one else can: I can be the most me possible. My worldview, my ideas, my storytelling, my intricacies, my personality ⏤ it’s all mine, and it’s what will make me stand out in a field of clones.


I’m sure I’m not alone on this one, but I’ve got faith in us for 2020.

Staying off my phone when out to dinner or when I’m with friends isn’t any real issue for me. The issue comes as “micro-procrastinations” or “productive-procrastination.”

Micro-procrastination: putting off important tasks in 2-10 minute bursts, but several times per day, which adds up to be significant.

Productive-procrastination: putting off “deep” tasks by doing “shallow” tasks instead. It feels like you’re getting work done, but you’re just busy, not productive. E.g., cleaning, reading, personal hygiene, planning, scrolling through Instagram doing “market research” or “connecting”

If you want to dive deeper on this topic, I highly recommend Deep Work and Digital Minimalism by Cal Newport.

QUESTION 3: How can I fix what’s not working for a better result? (“What specific things can I focus on next time?”)

Action step #1: Before doing anything, ask myself, “Am I doing this because want to? Or because I think I’m supposed to want to? Does it actually excite me?”

Rationale: I’ll be playing to my actual strengths and not just strengths I think I should have.

There’s also a large likelihood that I’ll be happier, more excited about work, and put forth more effort with experiences/projects that I genuinely enjoy.

Action step #2: Write down my 3 most important things to do for the NEXT day on an index card before I close my laptop.

Rationale: I struggle with “turning off” at night time and not feeling completely satisfied with my day’s work when it’s time to wind down. I’ve typically got a lot done, but not enough of the right things (busy, not productive).

So, to combat this, I have to win the day before it even starts.

I have to make my organization and planning as frictionless as possible. It has be so stupid simple and effortless that I would be ashamed to not do it.

Action step #3: Keep a running task list and a thoughts list. Divide one half of paper into “TASK LIST” and the other half into “THOUGHTS”.

Rationale: This is to cage my monkey mind. I’ve realized that my memory is terrible and if I don’t write it down I’m going to forget it.

One quote I love from the book Getting Things Done by David Allen:

“It’s a waste of time and energy to keep thinking about something that you make no progress on. There is no reason to ever have the same thought twice, unless you like having that thought.”

By having a running task list and thoughts list always close by, I should be able to alleviate some anxiety and overwhelm.

Write your own Personal Retrospective

OK, now you have an example of mine ⏤ it’s your turn.

Give yourself some time to think, reflect, and write. It should take roughly an hour, but you owe it to yourself⏤both past and future you⏤to take this seriously.

What went well? What could you improve on to make 2020 as good as you could possibly make it?

And the biggest question: what are you going to do about it?


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